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In 1996, her short-lived engagement on Thea led Norwood to star in her own show, the UPN-produced sitcom Moesha.Appearing alongside William Allen Young and Sheryl Lee Ralph, she played the title role of Moesha Mitchell, a Los Angeles girl coping with a stepmother as well as the pressures and demands of becoming an adult.The two-hour Wonderful World of Disney special garnered an estimated 60 million viewers, giving the network its highest ratings in the time period in 16 years, and won an Emmy Award for Outstanding Art Direction for a Variety or Music Program the following year.Fledgling producer Rodney "Darkchild" Jerkins was consulted to contribute to Norwood's second album Never Say Never, which was released in June 1998, and is also her best album.

In April 2015, Norwood made her Broadway debut in the musical Chicago.

The album earned Norwood two Grammy Award nominations for Best New Artist and Best Female R&B Vocal Performance the following year, and won her four Soul Train Music Awards, two Billboard Awards, and the New York Children's Choice Award.

In 1996, Norwood also collaborated with Tamia, Chaka Khan, and Gladys Knight on the single "Missing You", released from the soundtrack of the F. The single won her a third Grammy nomination in the Best Pop Collaboration with Vocals category.

In 2002, she starred in the reality series Brandy: Special Delivery, documenting the birth of her daughter.

Her third and fourth albums, Full Moon (2002) and Afrodisiac (2004), were released to critical and commercial success.

In the 2010s, Norwood received a critical and commercial resurgence.

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